going too look at another mini as my wife is dying for a convertible. I have a 2008 S hardtop manual trans, but is there anything specific I should look at on this model which is an automatic?

 

definitely, the auto is prone to poor shifting starting at early mileage like as soon as 20k. Look for harsh 1-2, 2-3 shifts, harsh downshift 2-1 and flair in 4th gear. Most symptoms occur once the tranny is hot (so after 20-30 minutes of city driving).
If the tranny is fine, count on doing a fluid change soon after buying to keep it going.
The top can have quite a few failure points so make sure it is working perfectly.
The rest is standard first gen Mini stuff like oil leaks, power steering failure, air bag light, broken seat tilt mechanisms, motor mounts, mushrooming strut towers, rusty exhaust and SC failure.
There are lots of things that can go wrong so be careful. On the plus side the motor is fairly robust. Get a warrantee if possible.
My wife loves her cabrio, but we did have to get the tranny valvebody repaired, thankfully under warrantee.